Triphenylphosphine → HCID 86637296, compound

HRID 1876876Notes

Reaction equation

HRID 1876876 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([C:13]3([CH2:20][C:21]#[N:22])[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]3)[CH:12]=2)[CH:5]=[CH:4][N:3]=1.[CH3:23][C:24]1[O:28][N:27]=[C:26](O)[CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([C:13]3([CH2:20][C:21]#[N:22])[CH2:18][CH2:17][CH:16]([O:19][C:26]4[CH:25]=[C:24]([CH3:23])[O:28][N:27]=4)[CH2:15][CH2:14]3)[CH:12]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 24781HymexazolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 86637294HCID 86637294, compound

Product 1

HCID 86637296HCID 86637296, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-4-hydroxycyclohexylacetonitrile (0.6 g, 0.00189 mol) in tetrahydrofuran (9 mL) was added 5-methylisoxazol-3-ol (0.22 g, 0.0023 mol), triphenylphosphine (0.594 g, 0.00226 mol), followed by diisopropyl azodicarboxylate (0.446 mL, 0.00226 mol). The mixture was heated at 70° C. overnight. After evaporating to dryness, the residue was purified on silica gel, eluting with 0 to 80% EtOAc in hexanes, to give the desired product. LCMS (M+H) 399.1.

Workup

  1. customAfter evaporating to dryness
  2. customthe residue was purified on silica gel
  3. washeluting with 0 to 80% EtOAc in hexanes

Sources & evidence

ORD record
ord-b335fdaa536841c2ae5d3140f959cf9f
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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